Holiday rentals in Chessington

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Top-rated holiday rentals in Chessington

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
An outdoor hot tub is situated on a wooden deck, surrounded by lush greenery. A seating area with a light-colored chair offers a comfortable spot to relax. Large sliding glass doors lead into the retreat, allowing for seamless indoor-outdoor access.
Shepherd’s hut
4.99 out of 5 average rating, 173 reviews

Lavish Retreat & Champagne 30mins Taxi from London

The Little Touch of Grey, provides an electric ambiance and the perfect setting for the elite of mind, who wants to reward both themselves and their partner. We are proud to share the latest addition to our portfolio with those who appreciate of all things bespoke. Included are; a complimentary bottle of Champagne, indoor & outdoor Jacuzzi, underfloor heating, sound system and salacious yet tasteful surprises throughout. For special occasions, use our secret compartment to add to your surprise.

Top guest favourite
The spacious bed is dressed in white linens, complemented by decorative pillows featuring tropical patterns. Gold sconces flank the bed, illuminating the unique textural wall with intricate patterns. A round mirror adds depth, reflecting the soft lighting in the cozy sleeping area.
Guest house
4.96 out of 5 average rating, 307 reviews

Ground floor studio with private entrance

A quiet, ground floor studio flat, fully self-contained, affording high levels of privacy & comfort, with freedom to come & go via your own front door at anytime day or night. Situated in a quiet, safe, leafy cul-de-sac in Cobham (dubbed UK’s Beverly Hills!) which offers: The Ivy, gastro pubs, boutique shops, Waitrose & more. Driving: 5mins to Oxshott station, 10mins to M25, 20mins to Guildford (or train). Airports: Heathrow (10miles), Gatwick (16miles). Trains to London Waterloo: 35mins.

Top guest favourite
The living area features high wooden beams and a large window allowing natural light. A comfortable sofa is placed alongside classic armchairs. A kitchen area with cabinetry is visible, complemented by a decorative lamp and houseplants. Soft textures enhance the cozy environment.
Cottage
4.99 out of 5 average rating, 110 reviews

Beautiful oak barn in peaceful countryside setting

Delightful detached barn crafted from French oak in a peaceful private lane on a gated country estate. Luxuriously appointed with full facilities for a short break or longer stay. Air Con. Free EV charging point. Many public footpaths close by. Local shops are only a 10 minutes stroll. Gastro pubs, restaurants and independent shops within easy walking distance. A short drive from M25 (J11). Fast rail links to London from Woking. LGBTQ+ friendly. Friendly Spaniel and Siamese cat on site.

Top guest favourite
A bright sitting room features a cozy sofa adorned with yellow cushions. A large mirror reflects natural light, while a dresser and a small cabinet provide convenient storage. A circular area rug adds softness to the floor, and windows are dressed with simple curtains.
Guest suite
5 out of 5 average rating, 127 reviews

Self-contained, double bed, clean and comfortable

Please read. A comfortable, clean uncluttered standard double bed annexe with en-suite, kitchenette and sitting room looking out onto the garden in a residential road, for 'single occupancy' only. NB. the annexe is not a 'day/holiday sanctuary' as life continues around it during the busy working day within a residential road. Most suitable for those working (regular hours) in the area as guest will be required to vacate the property daily between the hours of 11.00-16.00 or thereabouts.

Top guest favourite
The room features a spacious double Queen bed adorned with clean white linens. A bedside table with a lamp complements the bed. A small TV is positioned on a stand across from the bed, while natural light enters through a nearby window.
Guest suite
4.94 out of 5 average rating, 176 reviews

Studio, own access, self contained.

The room has it's own entrance door. It has a double Queen size bed, shower room and kitchen area (tea, coffee, cereal etc supplied) with fridge, microwave and single induction hob. There is a sofa, TV & table with two chairs. Our home is about a 15 minute walk to Claygate station. Trains direct to London Waterloo (35 mins) and Guildford. Claygate has local shops and a CoOp, several pubs and restaurants and we are close to a bus stop with a frequent bus service to Kingston for major shops.

Top guest favourite
The detached annex showcases a brick exterior with a pitched roof. A paved pathway leads to the entrance, bordered by potted plants. Lush greenery frames the property, and a gravel area provides additional parking and access to the surrounding garden.
Guest house
5 out of 5 average rating, 138 reviews

Peaceful & cosy detached annex with outdoor space

Situated within the grounds of a private property, set back from the road in a leafy residential part of Epsom. Welcome to our peaceful, detached annex offering flexibility, comfort and outdoor space. International guests will find us conveniently situated within 30mins drive of London Gatwick and Heathrow Airports (traffic permitting) and 40mins by train into central London. Ideal for those needing a base to enjoy the delights that Surrey has to offer or somewhere quiet to work from.

Top guest favourite
The exterior of the Georgian dwelling is framed by lush greenery, featuring a variety of plants and trees. A well-kept staircase leads to the entrance, showcasing the brick facade and charming windows. Natural light enhances the inviting atmosphere of the surroundings.
Flat
4.99 out of 5 average rating, 135 reviews

Clive House, Portsmouth Road, Esher, KT10 9LH

Nestled walking distance from Esher High Street the apartment is situated across the courtyard of Clive House, a Georgian dwelling built in the middle of the eighteenth century by Clive of India. The newly refurbished accommodation includes : living area, kitchen/ diner and ensuite double bedroom with a kingsize bed. Living includes a new compact and bijou fully fitted kitchen, dining area with wood burner, luxurious sofa and Smart HD TV/ Sonos sound bar as well as complimentary WiFi.

Guest favourite
A stylish cabin interior showcases a warm wood structure, featuring a cozy sleeping area with a neatly made bed. A round dining table is paired with two chairs, illuminated by soft lighting. An outdoor seating area is visible through the window, surrounded by wooden fencing.
Cabin
4.91 out of 5 average rating, 108 reviews

London & Surrey Cub House

Your own private stylish cabin, own entrance, self check-in. King-size bed, en-suite, kitchenette & private outside space. 8min walk to 2 stations into central London (Waterloo 25min, Wimbledon 15min). Good links to Hampton Court, Kingston upon Thames, Surrey walks and villages. Superloop 7 Bus (SL7) direct to and from Heathrow Airport, 1hour. Very quiet residential road with free parking. No more than 2 guest permitted at anytime on the property. No smoking/vaping on the property.

Top guest favourite
A spacious sleeping area features a soft, upholstered headboard and ample natural light from the glass doors leading to a deck. A table with two chairs is visible outside. Fresh towels are neatly arranged on the bed, framed by light wood flooring and neutral walls.
Guest suite
4.96 out of 5 average rating, 619 reviews

Lovely self-contained annex with shower room

Lovely, light spacious annex with en-suite shower room. It has a separate entrance and access to a deck. Off street parking is available. Situated in a quiet, tree-lined lane, it is a 5 minute drive to Horsley station which has a direct line into London Waterloo. Lots of lovely restaurants, pubs and cafes nearby for breakfast, lunch or dinner. There’s a mini fridge and microwave in the annex. PLEASE NOTE: ON BOOKING I’LL SEND DETAILED DIRECTIONS AND INFORMATION ON ACCESSING THE ANNEX.

Top guest favourite
The open plan living area features gabled ceilings and stylish furnishings. A comfortable sofa sits across from a galley kitchen with modern cabinetry. French windows open to a private patio garden, while natural light enters through sheer curtains, creating a bright and inviting atmosphere.
Home
5 out of 5 average rating, 128 reviews

Hampton Court: Spacious, Bright & Tranquil Annexe

Our newly renovated spacious 2 bedroom annex is situated in a wide tree lined road, a premier location just a few minutes walk away from the charming cafés, shops and restaurants of Hampton Court Village, Hampton Court Palace and local train station. Adjacent to but detached from our elegant Victorian family home, this bright and stylish space is tranquil and self contained and enjoys additional benefits of a private south facing patio garden and dedicated off street parking space.

Top guest favourite
A modern living area features a plush gray sectional sofa adorned with colorful pillows. A patterned area rug adds warmth to the space, while a wall mirror reflects light. Adjacent, a compact dining area is seen, with a small table and chairs, leading into an open kitchen.
Guest house
4.93 out of 5 average rating, 154 reviews

Private luxury apartment with free Secure parking

Outbuilding with front free parking (only 1 car per booking). Peaceful surroundings with west facing sun (longer days) and wildlife. Close amenities with 24 hour gas station and close shops near by, 7 mins to Epsom town and 6 mins to Chessington world of adventures (by car) and 30 mins trains straight to Waterloo. Very secure apartment as there is CCTV outside in the main house. You will truly enjoy this quiet luxury apartment. *Discount will be offered to returning guests*

Top guest favourite
A spacious loft room features a comfortable double bed with soft linens and neatly rolled towels. A cozy seating area includes two chairs and a small dining table. Natural light streams in from a skylight and window adorned with patterned curtains, contributing to a bright atmosphere.
Guest house
4.97 out of 5 average rating, 315 reviews

Quaint Self-contained Loft Studio nr Hampton Court

Quaint, quirky, clean and bright for you to relax in private, coming and going as you wish. Nestled in a safe, quiet area, perfectly situated for Hampton Court, Sandown Park Racing, Wimbledon Tennis, Bushy Park with its wild deer, the Thames and great shopping in Kingston. Breakfast included with pubs and restaurants nearby. Within walking distance of two railway stations, direct into London. Twickenham Stadium is just under 30 minutes away. Plenty of free on-street parking.

Popular amenities for Chessington holiday rentals

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Frequently Asked Questions

  • How much does it cost to stay in apartment rentals in Chessington?

    Experience the best of Chessington with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Chessington have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Chessington. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Chessington?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with a kitchen, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there vacation rentals with a dedicated workspace in Chessington?

    Yes! Work meets play with ease at over 10 vacation rentals in Chessington featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do apartment rentals in Chessington have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Chessington. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Chessington?

    Chessington has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Where should I stay in Chessington?

    Make yourself at home in Chessington by choosing from our most frequently booked neighborhoods. We have over 990 vacation rentals in Hook, over 120 vacation rentals in Malden Rushett, and over 2,970 vacation rentals in Chessington.

  • Are there pet-friendly vacation rentals in Chessington?

    Four-legged friends are welcome in Chessington. Choose from more than 10 vacation rentals for guests traveling with pets.

Quick stats about holiday rentals in Chessington

  • Total holiday rentals

    Explore 50 holiday rentals in Chessington

  • Nightly prices starting at

    Chessington holiday rentals start at £22 per night before taxes and fees

  • Verified guest reviews

    Over 1,310 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    50 of Chessington holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chessington rentals

  • 4.8 Average rating

    Chessington stays are highly rated by guests – averaging 4.8 out of 5!

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